A Practical Synthesis of (1S,2R)-1-Amino-2-indanol, a Key Component of an HIV Protease Inhibitor, Indinavir

Hiroshi Kajiro; Shuichi Mitamura; Atsunori Mori; Tamejiro Hirama

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A Practical Synthesis of (1S,2R)-1-Amino-2-indanol, a Key Component of an HIV Protease Inhibitor, Indinavir

机译：实用合成（1S，2R）-1-氨基-2-茚满醇，HIV蛋白酶抑制剂Indinavir的关键组分

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A synthesis of (1S,AR)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)-3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)--2-acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (+-)-2-acetoxy-1-indanone. Ketone (R)-3 was converted into 1 through an oxime formation and diastereoselective hydrogenation.

机译：HIV蛋白酶抑制剂的关键组分（1S，AR）-1-氨基-2-茚满醇（1）的合成是通过（R）-2-羟基-1-茚满酮（（R）-3）完成的，其通过容易地从D-（R）-苯丙氨酸获得的（R）-2-乙酰氧基-3-苯基丙酸的分子内Friedel-Crafts酰化制备。或者，通过（+-）-2-乙酰氧基-1-茚满酮的酶促拆分获得（R）-3。酮（R）-3通过肟的形成和非对映选择性氢化转化为1。

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《Bulletin of the Chemical Society of Japan》 |1999年第5期|共8页
作者
Hiroshi Kajiro; Shuichi Mitamura; Atsunori Mori; Tamejiro Hirama;
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正文语种 eng
中图分类化学;化学工业;
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1. A Practical Synthesis of (1S,2R)-1-Amino-2-indanol, a Key Component of an HIV Protease Inhibitor, Indinavir [J] . Hiroshi Kajiro, Shuichi Mitamura, Atsunori Mori, Bulletin of the Chemical Society of Japan . 1999,第5期

机译：实用合成（1S，2R）-1-氨基-2-茚满醇，HIV蛋白酶抑制剂Indinavir的关键组分
2. Lipase-mediated resolution of cis-1-amino-2-indanol, the key component of the HIV protease inhibitor indinavir [J] . A. T. Anilkumar, Kouhei Goto, Tomiki Takahashi, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 1999,第13期

机译：脂肪酶介导的顺式-1-氨基-2-茚满醇的拆分，这是HIV蛋白酶抑制剂茚地那韦的关键成分
3. Practical synthesis of (2s,3s)-3-amino-2-hydroxy-4-phenylbutyric acid, a key component of HIV protease inhibitors. [J] . Shibata N, Itoh E, Terashima S Chemical and Pharmaceutical Bulletin . 1998,第4期

机译：实用合成（2s，3s）-3-氨基-2-羟基-4-苯基丁酸，HIV蛋白酶抑制剂的重要组成部分。
4. A PRACTICAL SYNTHESIS OF KEY CHIRAL EPOXIDE INTERMEDIATES FOR PROTEASE INHIBITORS FROM L-ASCORBIC ACID [C] . Soon Mog So, Sang Min Lee, Kyoung Mee Seol International Carbohydrate Symposium . 2013

机译：L-抗坏血酸蛋白酶抑制剂的关键手性环氧化物中间体的实际合成
5. Design and synthesis of core structural intermediates for novel HIV-1 protease inhibitors and synthesis, biological activity and molecular modeling of novel 20S proteasome inhibitors. [D] . Avancha, Kiran Kumar Venkata Raja. 2006

机译：新型HIV-1蛋白酶抑制剂的核心结构中间体的设计与合成，新型20S蛋白酶体抑制剂的合成，生物学活性和分子建模。
6. Pairwise additivity of energy components in protein-ligand binding: The HIV II protease-Indinavir case [O] . Melek N. Ucisik, Danial S. Dashti, John C. Faver, -1

机译：蛋白质-配体结合中能量成分的成对加性：HIV II蛋白酶-茚地那韦案例
7. The HIV Protease Inhibitor Indinavir Impairs Sterol Regulatory Element-Binding Protein-1 Intranuclear Localization, Inhibits Preadipocyte Differentiation, and Induces Insulin Resistance [O] . Martine Caron, Martine Auclair, Corinne Vigouroux, 2001

机译：HIV蛋白酶抑制剂Indinavir indinavir损害甾醇调节元素结合蛋白-1顽核定位，抑制前脂肪细胞分化，并诱导胰岛素抵抗

A Practical Synthesis of (1S,2R)-1-Amino-2-indanol, a Key Component of an HIV Protease Inhibitor, Indinavir

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